A few months ago, I wrote about one of my favorite phrases used by Democratic politicians in Washington, D.C.: "Pay your fair share."
asserted
I → write → share
Politicians love saying wealthy Americans aren't paying enough.
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Americans → say → enough
The problem is the numbers tell a different story.
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numbers → tell → story
The top 1% of taxpayers already pay roughly 40% of federal individual income taxes.
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% → pay → taxes
The top 10% pay the overwhelming majority of taxes.
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% → pay → taxes
Because the debate isn't stopping at ordinary income taxes.
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debate → stop → taxes
Here are five more ways successful Americans could increasingly find themselves paying even more.
uncertain
themselves → find → more
But high earners already pay the highest federal marginal income-tax rate, plus state income taxes that can push combined marginal rates significantly higher in places like California and New York.
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that → pay → California
At what percentage does "fair share" officially become fair?
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share → become → ?
No political candidate will tell you that number.
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candidate → tell → number
Raise your capital gains taxes
Here's another Washington favorite.
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favorite → raise → taxes
This one is sneaky and likely the No. 1 tax angle to be attacked if political winds change in the White House.
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winds → attack → House
Sounds simple until you remember where investment capital comes from.
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capital → sound → where
People risk money starting companies, funding businesses, buying stocks and investing in real estate because they hope to earn a return.
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they → risk → return
You can tax that return more heavily.
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You → tax → return
Just don't pretend people won't change their behavior when you do that, because they will.
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they → pretend → that
3. Tax your wealth while you are living
Why wait until somebody earns money?
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somebody → tax → money
Some politicians want to tax wealth simply because someone owns it.
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someone → want → it
Imagine building a company worth $100 million but not having $100 million sitting in your checking account.
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million → imagine → account
Your business might be worth a fortune on paper while your actual cash is tied up inside the company.
uncertain
cash → tie → company
Now Uncle Sam wants a piece before you even sell it.
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you → want → it
California will tell us the first chapter of this story on the November ballot.
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California → tell → ballot
Take more when you die
America already has a federal estate tax.
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America → take → tax
For 2026, estates above the federal exemption can face a top estate-tax rate of 40%.
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estates → face → %
Some states can take another bite.
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states → take → bite
At what percentage does "fair share" officially become fair?
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share → become → ?
No political candidate will tell you that number.
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candidate → tell → number
You earn the money.
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You → earn → money
You pay income taxes.
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You → pay → taxes
You invest what's left.
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what → invest → ?
And when you die, the government may want another piece of what's still sitting there.
uncertain
what → die → piece
There’s a $15-million exemption today, but what if this reverts to 2000 levels, when the number was less than $1 million?
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number → ’ → levels
Imagine your kids, your heirs and your family having to pay 50% or more to the government when you die?
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you → imagine → government
How many times does the same dollar need to be taxed before everybody agrees it finally paid its fair share?
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it → need → share
States are getting into the game as well.
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States → get → game
Massachusetts has its millionaire surtax.
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Massachusetts → have → surtax
California has its own high-income surtax.
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California → have → surtax
Eventually, all those "little" taxes start looking pretty big.
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taxes → start → ?
Congress wrote the loopholes.
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Congress → write → loopholes
If Congress doesn't like a provision in the tax code, change it.
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Congress → like → it
…and 8 more, not listed.
The Aporia
